EP3557993A1 - Combinaison synergique d'ortho-phénylphénol et de bis-(3-aminopropyl) dodécylamine - Google Patents

Combinaison synergique d'ortho-phénylphénol et de bis-(3-aminopropyl) dodécylamine

Info

Publication number
EP3557993A1
EP3557993A1 EP17804332.9A EP17804332A EP3557993A1 EP 3557993 A1 EP3557993 A1 EP 3557993A1 EP 17804332 A EP17804332 A EP 17804332A EP 3557993 A1 EP3557993 A1 EP 3557993A1
Authority
EP
European Patent Office
Prior art keywords
aqueous
growth
dodecylamine
phenylphenol
aminopropyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP17804332.9A
Other languages
German (de)
English (en)
Inventor
Patrick T. FELDER
Emmanuelle Christine Yvon
Alessandro VEZZOLI
Maciej SZYMECZKO
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Publication of EP3557993A1 publication Critical patent/EP3557993A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms

Definitions

  • This invention relates to combinations of biocides, the combinations having greater activity than would be observed for the individual antimicrobial compounds.
  • combinations of at least two antimicrobial compounds can broaden potential markets, reduce use concentrations and costs, and reduce waste.
  • commercial antimicrobial compounds cannot provide effective control of microorganisms, even at high use concentrations, due to weak activity against certain types of microorganisms, or relatively slow antimicrobial action, or instability under certain conditions such as high temperature and high pH.
  • Combinations of different antimicrobial compounds are sometimes used to provide overall control of microorganisms or to provide the same level of microbial control at lower use rates in a particular end use environment.
  • synergy has been found to be an unpredictable phenomenon. Often like compounds display varying synergistic profiles when combined with a particular active.
  • synergistic antimicrobial composition comprising ori/20-phenylphenol and bis-(3-aminopropyl)dodecylamine (also known as BDA or diamine or triamine) (CAS registry number is 2372-82-9).
  • the invention further provides a method of inhibiting the growth of or controlling the growth of microorganisms in an aqueous medium, the method comprising the step of adding a synergistic antimicrobial composition comprising OPP and BDA.
  • antimicrobial compound refers to a compound capable of inhibiting the growth of or controlling the growth of microorganisms; antimicrobial compounds include bactericides, bacteriostats, fungicides, fungistats, algaecides and algistats, depending on the dose level applied, system conditions and the level of microbial control desired.
  • antimicrobial compound as used herein is synonymous with the term “biocide”.
  • microorganism includes, for example, fungi (such as yeast and mold), bacteria and algae.
  • Percentages of antimicrobial compounds in the composition of this invention are based on the total weight of active ingredients in the composition, i.e., the antimicrobial compounds themselves, exclusive of any amounts of solvents, carriers, dispersants, stabilizers or other materials which may be present.
  • OPP ori/20-phenylphenol
  • OPP is sodium ori/20-phenylphenate (also known as NaOPP) (CAS registry number is 132-27-4 (and 6152-33-6)).
  • BDA bis-(3-aminopropyl)dodecylamine (also known as diamine)
  • ratios are the herein to be "X:l or higher,” it is meant that the ratio is Y:l, where Y is X or greater, and when a ratio is the herein to be “X: 1 or lower,” it is meant that the ratio is Z: 1, where Z is X or less.
  • X:l or higher it is meant that the ratio is Y:l, where Y is X or greater
  • X: 1 or lower it is meant that the ratio is Z: 1, where Z is X or less.
  • the present invention is a composition that contains both OPP and BDA. It has been surprisingly found that compositions that contain both OPP and BDA are synergistically effective as biocides.
  • the weight ratio of the OPP to BDA is from 1: 1 to 100:1 alternatively from 1:1 to 10:1 and further alternatively from 10:1 to 100:1.
  • the antimicrobial combination of this invention is useful for inhibiting the growth of or controlling the growth of microorganisms in an aqueous medium.
  • aqueous media include but is not limited to industrial water and water containing/contaminated media, such as cooling water, air washer, heat exchangers, boiler water, pulp and paper mill water, other industrial process water media such as: ballast water, wastewater, metalworking fluids, oil and gas, latex, paint, coatings, adhesives, inks, tape joint compounds, pigment, water-based slurries, personal care and household products such as detergent, filtration systems (including reverse osmosis and ultrafiltration systems), toilet bowel, textiles, leather and leather production system, or a system used therewith.
  • the antimicrobial composition is used as an in-can preservative.
  • the amount of the biocide combinations of the present invention for inhibiting the growth of or controlling the growth microorganisms is from 10 ppm to 5,000 ppm active ingredient.
  • the active ingredients of the composition are present in an amount of at least 20 ppm, alternatively at least 50 ppm, alternatively at least 100 ppm, alternatively at least 150 ppm, alternatively at least 200 ppm.
  • the active ingredients of the composition are present in an amount of no more than 2,000 ppm, alternatively no more than 1,000 ppm, alternatively no more than 500 ppm, alternatively no more than 400 ppm, alternatively no more than 300 ppm, alternatively no more than 250 ppm, alternatively no more than 200 ppm, alternatively no more than 100 ppm, alternatively no more than 50 ppm. Concentrations mentioned above are in a liquid composition containing the biocide combinations.
  • the present invention also encompasses a method for inhibiting the growth of or controlling the growth of microorganisms in the use areas described above, especially in in- can preservative applications, by incorporating the claimed biocide combination into the materials.
  • composition of the present invention contains OPP and BDA. It is contemplated that some embodiments may contain one or more additional antimicrobial compound.
  • the synergism of the biocides combination of the present invention was determined using the Minimum Inhibitory (MIC) test method described by Kull, F.C., et. al in Applied MIC) test method described by Kull, F.C., et. al in Applied MIC
  • QA minimum inhibitory concentration in ppm of compound A acting alone
  • Qa minimum inhibitory concentration in ppm of compound A in the mixture.
  • QB minimum inhibitory concentration in ppm of compound B acting alone.
  • Qb minimum inhibitory concentration in ppm of compound B in the mixture.
  • the Minimum Inhibitory Concentration Test is designed to evaluate the lowest concentration of a biocide, biocide blend or biocide combination to prevent bacteria growing in a defined broth.
  • MIC Minimum Inhibitory Concentration
  • the MICs of the single biocides NaOPP and BDA as well as of combinations of these two actives (all in TSB) in 3 different ratios (1 : 1 ; 10: 1, 100: 1) were estimated against each of the 4 microorganisms Staphylococcus aureus (DSMZ#799), Pseudomonas aeruginosa (DSMZ#939) and Candida albicans (DSMZ#1386), Pseudomonas putida, respectively.
  • the test was executed with a Hamilton MLStarPlus robot using automated turbidity reading with BioTek Synergy H4 plate reader.
  • Biocide systems were prepared in 2.2 ml deep well plates by transferring and diluting biocides from stock solutions to first rows of the plates. The concentrations of biocides in stock bottles were adjusted to be 20x more concentrated than the highest desired concentration.
  • the culture was maintained as a glycerol stock at -80°C in cryovials.
  • a cryovial was thawed and then 100 ⁇ spread on a TSA agar plate. After incubation for 1 day at 30°C the bacteria were harvested with buffer at pH 7.3. A total viable count on TSA plate was carried out and bacterial suspension was diluted in buffer in order to deliver ⁇ 2xl0 7 CFU/ml.
  • the cultures were maintained as glycerol stocks at -80°C in cryovials, are thawed and then 100 ⁇ spread on MEA (malt extract agar) petri dishes.
  • the yeast strain plates were incubated at 28 °C for 1-2 days then harvested with buffer pH 5.0.
  • the inoculum was prepared.
  • test sample (190 ⁇ ) was inoculated with the 10 ⁇ of microbe suspension to provide a level of ⁇ 1 x 10 6 CFU/ml of the bacteria species and ⁇ 1 x 10 5 CFU/ml of the yeast species.
  • test samples were mixed and incubated at 30°C for 2 days (48 hours) when tested against bacteria and 3 days (72 hours), respectively, when tested against yeast.
  • the MIC did't be determined as there was still growth at the highest tested concentration of the active.
  • the MIC indicated is an estimation and represents the next higher concentration (1.3x) than tested. It is likely that the actual MIC is greater than the value indicated.
  • the Synergy Index is calculated based on a theoretical MIC value of BDA (see a ) or on theoretical MIC values of NaOPP:BDA(10: l); the actual synergy index is less than or equal to the value calculated in the table.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition antimicrobienne synergique contenant de l'ortho-phénylphénol et ses sels et de la bis-(3-aminopropyl)dodécylamine. L'invention concerne également un procédé d'inhibition de la croissance ou de régulation de la croissance de micro-organismes dans un milieu aqueux et un produit à base aqueuse.
EP17804332.9A 2016-12-21 2017-10-25 Combinaison synergique d'ortho-phénylphénol et de bis-(3-aminopropyl) dodécylamine Withdrawn EP3557993A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201662437364P 2016-12-21 2016-12-21
PCT/US2017/058178 WO2018118206A1 (fr) 2016-12-21 2017-10-25 Combinaison synergique d'ortho-phénylphénol et de bis-(3-aminopropyl) dodécylamine

Publications (1)

Publication Number Publication Date
EP3557993A1 true EP3557993A1 (fr) 2019-10-30

Family

ID=60452728

Family Applications (1)

Application Number Title Priority Date Filing Date
EP17804332.9A Withdrawn EP3557993A1 (fr) 2016-12-21 2017-10-25 Combinaison synergique d'ortho-phénylphénol et de bis-(3-aminopropyl) dodécylamine

Country Status (5)

Country Link
US (1) US20190364890A1 (fr)
EP (1) EP3557993A1 (fr)
CN (1) CN110087465A (fr)
BR (1) BR112019012594A2 (fr)
WO (1) WO2018118206A1 (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1928192A1 (de) * 1969-06-03 1970-12-10 Goldschmidt Ag Th Synergistisches biocides Gemisch
GB2354771A (en) * 1999-10-01 2001-04-04 Mcbride Ltd Robert Bactericide combinations in detergents
EP1772055A1 (fr) 2005-10-04 2007-04-11 Rohm and Haas France SAS Compositions microbicides synergiques comprenant une N-alkyl-1,2-benzoisothiazolin-3-one
DE102005048955A1 (de) * 2005-10-13 2007-04-26 Lanxess Deutschland Gmbh Wirkstoffgemische aus OPP und Aminen
DE102009048189A1 (de) * 2009-10-02 2011-04-07 Schülke & Mayr GmbH Lagerstabile mikrobizide Konzentrate und deren Verwendung als Konservierungsmittel
DK2596702T3 (en) * 2011-11-25 2015-08-10 Omya Int Ag A method for stabilizing the bacterial content of the aqueous ground natural calcium carbonate and / or precipitated calcium carbonate and / or dolomite and / or surface-treated calcium carbonate-comprising mineral products
GB2501341B (en) * 2011-12-29 2014-10-22 Byotrol Plc Anti-microbial composition
FR3003129B1 (fr) * 2013-03-14 2016-02-26 Mexel Ind Composition biocide et procede de traitement de l'eau ou de surfaces en contact d'eau

Also Published As

Publication number Publication date
WO2018118206A1 (fr) 2018-06-28
CN110087465A (zh) 2019-08-02
BR112019012594A2 (pt) 2019-11-19
US20190364890A1 (en) 2019-12-05

Similar Documents

Publication Publication Date Title
JP7064030B2 (ja) 相乗的抗微生物組成物
US10709129B2 (en) Synergistic combination of bis-(3-aminopropyl)dodecylamine and sorbic acid
CA2956308C (fr) Composition antimicrobienne synergique
US8722713B2 (en) Synergistic antimicrobial composition of 1,2-benzisothiazolin-3-one and tris(hydroxymethyl)nitromethane
EP3557993A1 (fr) Combinaison synergique d'ortho-phénylphénol et de bis-(3-aminopropyl) dodécylamine
US10674729B2 (en) Synergistic combination of 3-IODO-2-propynyl-butylcarbamate and diamine
US20170086461A1 (en) Synergistic antimicrobial composition
AU2013231143B2 (en) Synergistic antimicrobial composition

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20190619

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
18W Application withdrawn

Effective date: 20200302